Maybe I should stop rambling.
Suffice it to say, it took some time for me to find anybody worth screwing.
I did, of course, at last- some shirtless douchebag, a few years older than me, but he had a hot body, and I felt fairly confident there was a cock below the belt to match it. I could put up with whatever shitty personality might come along with it to let him fuck me up the asshole for a night.
I clicked on his profile, and began to compose a straightforward enough message for him:
“I'm looking for something a little different...”
Chapter 3
It's still a little hard for me to believe that I'd never tried anal sex up to this point in my life. Like, you would imagine that I would have had some manipulative asshole of a boyfriend before now who'd tried to convince me that it wasn't that bad, and that I hadn't ever gotten curious about it before now.
Well, maybe I was curious. But I just couldn't fathom the prospect of something that large or ferocious being jammed up my innocent little bunghole.
So, it was with butterflies in my chest and my sphincter clenched into a knot that I knocked on the stranger's door, the night black around me, the only illumination the lights from the street lamps and that which poured through the few houses whose occupants were still awake.
He opened the door, and smiled.
I was apparently just what he was hoping for...
Things moved quickly.
We went straight to his bedroom, and the two of us fell onto his bed almost immediately, making out on top of the covers, melting into one another's mouths like candy, his lips dissolving into mine, our tongues swirling and lapping and licking and sucking, wrestling fiercely as the saliva rolled back and forth between our mouths...
I've got to say, it wasn't just the butt sex that had had me nervous. The idea of springing into sex with a stranger after a year of erotic dormancy had me pretty on edge, and I had a lot of performance anxiety about the idea of the whole situation. But, as it turned out, riding a cock was pretty much just like riding a bike.
Some things, you just don't forget...
The two of us rolling around, making out on his bed definitely thawed me out quite a bit as far as that goes.
He began to touch me through my clothes, cupping my breasts, and reaching up beneath my skirt, pushing his fingers into my pussy through my panties, at which point I had to pull away gasping.
He smiled at this, and I could tell by the look in his eyes that he enjoyed tormenting me.
He pinched a little bit harder, filling me with a bit of pain, making me whimper just to contain the sensation, but of course this was only a foretaste of the agony I was about to put myself through.
We began to undress one another, tearing our clothes off furiously. I hooked my fingers into the hem of his t-shirt, running my hands up along the terrain of his sweat-soaked muscles as I stripped him to his bare chest, trickling up his six pack abdominals, tracing out the cleavage of his pecs with my fingertips, at last pulling the article off altogether, and staring like a kid in a candy store at the sparkling form of that sex god's body, following the rippling flanks back down along him with my eyes, transfixed upon the sharply carved V-lines of his Adonis muscles, pointing like a glorious arrow on a treasure map to the wonderful prize down below...
He started peeling me out of my own clothes like a banana, brusquely pulling my blouse up over my head so that my tits bounced severely with the removal of the fabric. He massaged my titties for a little bit, pressing them around and around and around on my body in slow, loving circles. I tilted my head back and sighed, having forgotten how truly wonderful the touch of a man could be, and his fingers trickled down along my body like rain seeping down the form of a statue after a storm, from my breasts, to my abdomen, grasping my belly, streaking around my sides and making me squirm as he touched the small of my back, then letting his hands sink into the waistband of both my skirt and panties, his palms grazing warmly against my flesh. He peeled the fabric down off of me, running down along my thighs, to my knees, all the way down to along my ankles, so that I was naked from the waist down, still wearing my bra up top.
“Bend over,” he commanded, and I quickly obeyed, shivering slightly, crawling across the bedspread on my hands and knees like an animal, spreading my cheeks, so that my anus blossomed wide as a flower for picking, and the floral pink folds of my pussy down below it shimmered like a fish out of water.
I shrieked.
I swear to God, I'd been anticipating being fucked up the ass to be a painful as hell experience, but I hadn't expected the precursor of anilingus to be nearly as fucking traumatizing as the main event. I guess maybe it was the fact of not expecting it that got me, but shit... Have you ever had someone stick their tongue up your asshole without warning you first?
Or at all, for that matter?
It's a rather analogous (ha) sensation to being given a wet willy, but... Well, up the tooshie instead. Either way, if you're not expecting it, it's one hell of a shock. I mean, I enjoyed having my pussy eaten out just fine, it was just... I dunno...
Hell... My first rim job... I would have to add this to my scrapbook when I got home.
I could feel my ass shaking around his bobbing head, but as he licked, swirling his tongue around my sphincter, lapping me up, spitting into my ass occasionally, I began to limber up. I wouldn't say it was straightforward pleasure at any point, but there was something about the humiliation of it, the degradation, both of himself and me, that I loved. He started massaging my ass cheeks, kneading the flesh of my rump like dough, digging his fingers deep into my skin, eventually reaching beneath me to massage my pussy as well, doubling up the sensation.
And I started to moan.
Something was happening- I wasn't sure what, given how new this was to me. But it was something...
I barely had time to register it, though, before his face had disappeared from my ass.
I struggled to catch my breath, my breasts heaving rather intensely, and WHAM!
I felt the palm of his hand strike against my ass like thunder, sending a jolt of pain through my body that I'd not at all been expecting.
I hadn't really considered the fact that when all the action was going on behind you, you were inevitably in for a butt load of surprises (ha!)
He smacked me several more times, harder and harder and harder, watching my cheeks jiggle until they settled back down again, and then smacking them once more, again and again and again and again.
At last, once my butt looked like a baboon's with the amount of red handprints cascading across its hills, he relented, and I heard the rustle of fabric as he stripped down out of his shorts.
I braced myself, squinting, sort of wanting to cry to be honest, wishing I had something to bite down onto so I didn't chew my tongue off from the pain I was about to receive.
I heard the great fart of lubricant being pumped from its tube into the palm of his hand, and the sound just kept coming and coming and coming, making me envision a child squeezing the entire tube of his toothpaste onto the bathroom floor out of sheer curiosity, and I knew from the immense quantity of the stuff he must be accumulating in his palm at this point that I was truly and absolutely fucked.
At long, long last, the cap clicked shut.
I shrieked as he slapped his palm against my asshole, smacking the glob of icy cold lube into my anus, and smearing it around, his finger hooking into the rim and pushing it inside, and I could feel my nervous sphincter clenching shut around his fingertips as though trying to swallow him up, preventing him from being able to penetrate me with anything worse.
But of course, it didn't work.
I said a last, terrified prayer to the Virgin Mary, suddenly very much admonishing her decision to remain chaste, thinking she must surely have been the smartest woman ever born for the fact.
I felt his heat pressing up against me from behind.
A fleck of raging heat cut through the ice of the lube, and
something tight balled up in my throat.
I held my breath.
The tip of his erect penis melted through the rim of my sphincter, which was fighting him angrily, trying foolishly to close up and keep him out at all cost, but to no avail.
“Oh, God... Oh, God...” I said, preparing myself, flexing my spine back up toward him, but knowing it wouldn't do any good.
He slid the long, endless curved blade of his erect penis into the tight juicy confines of my anus, inch by inch by fuck fuck fucking inch, feeling more like mile after mile after mile, each additional stretch pushing apart the walls of my anus to a degree that was agonizing, unbearable, and left me screaming, “Fuck, fuck, fuck, fuck, fuck...”
And each time I thought that must surely be all he had left, that he would press down and start pulling back again to begin thrusting, more and more and more of him just kept coming, more and more and more, unrelenting, piercing my ass like an Amish man driving his pitchfork into a bail of hay (three for three!)
And finally, when I thought for fucking certain I was going to go ballistic from the pain, I felt his clean shaven pubes press down against my ass cheeks.
He held himself there, for several long, eternal seconds, getting used to the poorly ventilated heat of my dainty little bunghole, and meanwhile making me tremble like an earthquake to my absolute fucking core.
And he pulled himself slowly, slowly, slowly back out of me, building up suction as he curved painfully back out, giving me some faint relief, but not nearly enough, given that all I had the prospect of looking forward to was his agonizing return once more.
And he pushed back in, in in in in in, “Oh God oh God oh God,” back all the way up inside me, then back out, repeatedly, innnnnnnnn, ouuuuuutttttt, innnnnnnnn, ouuuuuutttttt, and always, no matter how used to it I should reasonably have been becoming, a river of profanities, obscenities, and blasphemies came tumbling through my lips on behalf of his sodomy, “Oh God, oh fuck, oh shit, oh damn, oh hell, oh fuck, oh fuck, oh fuck, oh FUCK!”
I started slamming the palm of my hand against the bed, sucking in as much air as I could to withstand the pain, my fingers clenching into the bedspread as he slowly fucked me, sweat beginning to pour in buckets down my skin.
And he started fucking me more rhythmically, pumping and humping and thrusting, his cock churning me into a mushy pulp, my body releasing a series of short anal queefs as he pumped the air out of me, and I knew through my own pain how much pleasure it must be giving him to fuck me like this, the suction building up hotly as he pulled back out of that little black pit, cool air blasting him as he pushed back in, stretching me cruelly apart.
And I felt tears running down my cheeks, the pain so horribly welled up in my throat that I thought I might suffocate, and I wondered why the fuck I'd ever wanted this?
And then he tore into me.
His cock jackhammered my anus at an intense, furious pace, his balls swinging wildly in their nut sack, slapping my pussy down below with the force of his movements, dark, wicked, animalistic, pumping as ferociously as a mechanical piston into a shaft, our sweat soaked bodies slapping together in loud explosions of noise, KLAP, KLAP, KLAP, KLAP, KLAP, my tits banging against my chest as they swung about wildly from my body, my head spinning as I roared with pain, “FUCK, FUCK, FUCK, FUCK, FUUUUUCK!”
WHAM!
It was all over.
He crammed himself so deeply into me I thought he might come popping out through the other side, ejaculating wildly into my body, his cum streaming up my ass in long, sticky torrents, coating the dark pink tunnel with his hot seed, so thick and so abundant it came rolling back out just as quickly as it could enter, spilling from one hole into the other, coating the lips of my vag, and dripping onto the bedspread.
I was dying, I was dying, I was dying-
And then I wasn't anymore.
The pain was so intense, so unbearable, so absolutely horrifying that my body somehow transcended it, shooting me past the threshold of my agony, and sending me spiraling like a fallen rocket into the great fiery burst of an anal orgasm, the first in my life, and one so intense and so mind blowing that I started seeing stars, my body shaking, my limbs twitching like mad, every last fucking inch of my body convulsing with pleasure.
By the time he pulled out of me, with a loud, suctioned POP that let another big glob of his cum spill from my body, the bed beneath me was soaked with perspiration, and I curled my sweaty limbs into a fetal position, my body still shaking with that ungodly cocktail of sensations, my head spinning like a mad woman's.
One item down, and nine to go.
By the time this was all over, I thought for the first time, there was a reasonable chance that this to-screw list of mine might just be the death of me...
TO BE CONTINUED...
Milf And Chocolate
One
Alyshia didn't like new neighbors.
Or, well, maybe that wasn't quite accurate.
Maybe it was more along the lines that new neighbors didn't like Alyshia. And not all new neighbors. The problem, in reality, was that certain new neighbors tended to really, really, really like Alyshia. In particular- husbands, boyfriends, teenage boys... And it was always the women in their respective households who developed some understandable hostility toward Alyshia for the fact.
She couldn't help it, though, really. In spite of herself, she always found herself making eyes at whatever specimen of masculine perfection that happened to grace the presence of her block, bedroom eyes, specifically, fierce, deep, and penetrating, like the look a tiger gives its prey right before it devours it, a look that says, “You are mine, and there's nothing you can do about that... And trust me, you don't want to resist. You want to let it happen... I promise you'll enjoy it as I tear you to shreds...”
Tiger? Perhaps cougar would be the more adept choice in large feline in Alyshia's case.
Invariably, Alyshia was old enough to be the mother of any of her romantic conquests, and the mere thought of it aroused her beyond belief. She'd never had kids, and somehow this took away from any perceived “wrongness” of her predatory nature in her mind. She guessed she could understand why mothers and girlfriends and wives disliked her, but she didn't really see things from their perspective. Life was too short to worry about things like age and social propriety. Age was just a number, and social propriety was for people with sticks up their asses- excuse her French.
She would rather enjoy life with something up stuck up her ass, thank you very much...
Alyshia was the type of woman who should have known better at this point in her life but never really did seem to know better, and felt all the better off for the very fact of not knowing better. Although age was only a number, Alyshia's number was forty-two- about the time when some women tend to wind down their sexual careers and settle in for more than half a lifetime's physical dormancy, believing that that point in their life was good and over, and that that was that was that was that.
But not Alyshia.
For Alyshia, forty-two was the new eighteen, and she was enjoying herself and life more now than she ever had during her actual young adulthood, at the time when you're actually supposed to spread your legs like wildfire in order to get all the fun distractions in life out of the way while you're young. Alyshia was a woman like fine wine, improved with age, more delectable, more experienced, more confident and more enthusiastic to take control of things in the bedroom.
Not to mention, more adept at luring her innocent young prey...
The reason women hated her so much was that Alyshia was like a Venus flytrap, snapping up the young men in her life and devouring them, feeding off their energy, and always hungry for more, more, more... The women around her all thought that to a cougar such as her, all of these flings with young, innocent cubs were an act of desperation- or rather, they wanted to believe that, and that somehow the fact that their men all flocked to her with hypnotized eyes was because of her sad, middle-aged appeal for physical sym
pathy. That made it a little more bearable than the truth, which was that Alyshia, at forty-two, was in the prime of her sensuality, her charms more seductive and eroticism more acute than it had ever been or ever would be for the women around her whose men she devoured.
She'd always been a beautiful woman, and this, too, amplified and became more delicate with age. More fragile, and therefore more irresistible. Trampy blonde hair. Chaotically blue eyes that could rip you apart if you stared at them for more than an accidental instant. Caramel skin, tan and delectable, smooth and curvaceous as the rolling dunes of the Sahara, with a few lines here and there demarcating her transition to greater maturity, but serving as beauty marks rather than detractors from her feminine wares.
She'd also always been a major flirt- a fact, similarly, that was made abundantly more intense in her forties, so that every move she made made the men she wanted want her. Every sway of her hips in some ludicrously tight black dress, hugging her curves, her body rippling, her ass melting men's hearts as it rotated, step by step by step. Every flick of her hair, as every bit the trampy blonde eighteen year old she would always be at heart, and every flutter of her eyelashes that filled men with an equal and appropriate lust for her in return.
She laughed at jokes that weren't funny, she made men who weren't special at all feel special, and then she made them feel like shit, like animals, clawing them apart just as she'd built them up, tearing them limb from limb from limb, consuming whatever was left- and always, always, always, the men loved it. It made them feel like the men they wanted to be, and yet somehow not like men at all- like wards in her care almost, like they were being mothered, all of them as though they had some bizarre Oedipus complex that they could only see fulfilled through this luscious, curvaceous, and more than accommodating woman, this blonde bombshell, this MILF next door...
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